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Novel organosoluble polyamides with phthalimide pendant group: Synthesis, physical and thermal characterization

H.Mighani, H.Nasr Isfahani, S.Mighani

Adiamine, 4-(4-phthalimidophenyl)-1,2,4-triazolidyne-3,5-diamine (UD) as urazolediamine was synthesized in 8 steps from 4-nitrobenzoic acid. The diamine was characterized using FTIR, 1HNMR and melting point. Then it was used to prepare novel polyamides. Two novel phthalimide-containing aromatic–aliphatic polyamides, polyurazolterephtaloyl (PUT) and polyurazolsebacoyl (PUS), were prepared from the new diamine. The low temperature solution polycondensation of diamine with two aromatic and aliphatic diacid chlorides afforded diamine-containing polyamides with inherent viscosities of 0.32 and 0.36 dl/g in H2SO4 at 25 °C. Polyamides were generally soluble in a wide variety of different solvents such as dimethyformamide (DMF), N-Methylpyrolidone (NMP), tetrachloroethane (TCE), dimthylsulfoxide (DMSO) and H2SO4. Thermal analysis showed that these polyamideswere practically amorphous and exhibited 10%weight loss at about 250 °C. The glass transition temperatures (Tg) of the polymers were in the range of 144–183 °C. The temperatures at 10% weight loss (T10%) fromtheir thermogravimetric analysis curves were found to be in the range of 251–275 °C in nitrogen atmosphere.